Page 5 | To be shocked that my good friend, 37, is seeing a 66 year old lady?

darksideofthetoon · 2026-06-28T18:59:37+00:00

Had a few beers with a good friend recently and got a bit tipsy and we got into his dating life. He told me that he’s been seeing a 66 year old grandmother. He is only 37 for reference. They met via online dating. To be clear, there is nothing wrong with this but I’m just a bit shocked to be honest. He says that they enjoy each other’s company and there is no intention of it developing into anything more. My friend has always dated younger women and not short of female attention at all. It’s all good right?

Gettingbysomehow · 29/06/2026 21:28

Where can I find one?

Original poster

darksideofthetoon · 29/06/2026 21:28

SemiRetiredLoveGoddeess · 29/06/2026 21:20

What's wrong with this. Maybe she just wanted some young fresh meat. Or a friend with benefits.

Lets face it. Most 66 year old men are hardly Sex Gods. Are they!

Go for it lady

I started with my thread by saying it’s not wrong. Of course it’s not. But it took me by surprise.

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AJLOAL · 29/06/2026 21:26

TheBlueKoala · 29/06/2026 21:14

Do you never look at him and think "he could be my son?"

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Not at all and he doesn't look at me and think I'm a mother figure either.

Original poster

darksideofthetoon · 29/06/2026 21:25

walkingmycatnameddog · 29/06/2026 21:23

When I was in my sixties a man I worked with had a serious’crush’ on me. Even my husband could see it, the guy made no secret of it. He was 30. Younger than our son. It wasn’t funny, but it was weird. Difficult as we worked together. Came to the house too. I say crush because that’s what my husband called it. Especially as this guy frequently told my husband he was punching… We moved counties not because of him obviously but because of that we completely lost touch. I’d forgotten about it until I read this thread.

Hope this thread has not stirred any bad emotions for you.

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AgentPidge · 29/06/2026 21:25

TheBlueKoala · 29/06/2026 21:14

Do you never look at him and think "he could be my son?"

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I fancy blokes who ARE the same age as my son. So what? They're not my son!

PenelopeJoanSterling · 29/06/2026 21:25

GrumpyButOk · 29/06/2026 21:23

So it boils down to two single consenting adults happy spending time together and having sex with no long-term commitment. Why is this even a thread?

usually its the age gap, as in societys view it seems only the rich and famous should have age gaps, eg cher, madonna, etc

Draytoncb · 29/06/2026 21:24

It's nobody's business

GrumpyButOk · 29/06/2026 21:23

So it boils down to two single consenting adults happy spending time together and having sex with no long-term commitment. Why is this even a thread?

Original poster

darksideofthetoon · 29/06/2026 21:23

Peachperfect · 29/06/2026 18:19

Could she be his sugar mumma? Genuine question

Nah, discussed this earlier. He’s well off and generous so not in it for money.

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walkingmycatnameddog · 29/06/2026 21:23

When I was in my sixties a man I worked with had a serious’crush’ on me. Even my husband could see it, the guy made no secret of it. He was 30. Younger than our son. It wasn’t funny, but it was weird. Difficult as we worked together. Came to the house too. I say crush because that’s what my husband called it. Especially as this guy frequently told my husband he was punching… We moved counties not because of him obviously but because of that we completely lost touch. I’d forgotten about it until I read this thread.

AgentPidge · 29/06/2026 21:22

Manifoldoptions · 29/06/2026 19:30

She may appear so and so might he….but appearances can be very deceptive. It doesn’t matter how he appears but if she appears to be wealthy I’d be more cynical. You can try to guess but it’s really not possible to guage other people’s wealth. No way a young man would be up for it with a woman that age in my opinion unless he thinks he’s up for a cut. Sorry - very very cynical…..

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Ageist much? It can be about being attracted to someone's personality, humour, life experiences... Not just because you think they're rich.

PenelopeJoanSterling · 29/06/2026 21:22

riversofjoy · 29/06/2026 21:20

You would date someone aged 18 when you are 48 and you don’t find that problematic in any way? 😳

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for some people it depends on the nature of the relation and who chased who, eg the younger one chasing the older one,

not saying its right because morally it is jesus christ but they are both adults as some would say

SemiRetiredLoveGoddeess · 29/06/2026 21:20

What's wrong with this. Maybe she just wanted some young fresh meat. Or a friend with benefits.

Lets face it. Most 66 year old men are hardly Sex Gods. Are they!

Go for it lady

riversofjoy · 29/06/2026 21:20

AlgaeDreams · 29/06/2026 21:00

In which way do you see the power balancing? Interesting.

Not every relationship is about a power balance... The balance of power.

I've never actually had a relationship where that occurred to me.

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You would date someone aged 18 when you are 48 and you don’t find that problematic in any way? 😳

PenelopeJoanSterling · 29/06/2026 21:20

Rpop · 29/06/2026 21:19

I know. But in reality, it does present as an additional challenge in some cases. Let’s just say a very large age gap isn’t a protective factor…but I’m sure lots of relationships with large age gaps do work and are all the stronger for it. But it is unusual.

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but it seems unusually because its not on the daily media daily then it would be the norm etc

Rpop · 29/06/2026 21:19

PenelopeJoanSterling · 29/06/2026 20:02

even if you were brought up in different eras, you can still connect via hobbies etc, even same age gap relationships does not auto mean compatibility etc

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I know. But in reality, it does present as an additional challenge in some cases. Let’s just say a very large age gap isn’t a protective factor…but I’m sure lots of relationships with large age gaps do work and are all the stronger for it. But it is unusual.

TheBlueKoala · 29/06/2026 21:14

AJLOAL · 29/06/2026 20:18

I'm 57 and seeing a 38 year old man. No one's business but ours.

Do you never look at him and think "he could be my son?"

TheBlueKoala · 29/06/2026 21:11

darksideofthetoon · 28/06/2026 20:06

I have never seen this and seen a lot of things. Yes, I know some guys go for older women but the age gap is very large.

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I think it's weird. To be friends is one thing, to date it irks me. But at the end of the say they are consenting adults and can do whatever they want.

Appleseason · 29/06/2026 21:10

It’s weird, but they are two consenting adults. So I would leave them to it, to each their own.

AlgaeDreams · 29/06/2026 21:05

Beeloux · 29/06/2026 20:38

As I said, you do you.

I divorced my xh for such nonsense when I was as 24 and he was older than me.

No regrets.

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And by the time you are 33 you'll have a wealth of life experience, divorce being one, that you didn't have in your early 20s or teens.

AlgaeDreams · 29/06/2026 21:00

riversofjoy · 29/06/2026 19:30

But people havent defined that, they have merely said 30 years?- no problem.

I disagree. I think there is something very wrong if you have to date someone 30 years younger than you. It shows a power balance that indicates something very wrong

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In which way do you see the power balancing? Interesting.

Not every relationship is about a power balance... The balance of power.

I've never actually had a relationship where that occurred to me.

PintofFizz · 29/06/2026 20:56

SkippitySkoppity · 29/06/2026 20:55

I think they're referencing the film where Emma T plays a middle aged widow who engages the services of a hot young male sex worker.

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Ahhh thanks.

PintofFizz · 29/06/2026 20:56

Beeloux · 29/06/2026 19:41

You do you.

Personally I grew up in a culture where the husband provides. I find men who leech off woman unmasculine.

That’s just my personal opinion though.

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How about relationships where the couple are equal. Both contribute equally or sometimes he contributes more, sometimes she contributes more. I'm guessing a lot of relationships are like that.

SkippitySkoppity · 29/06/2026 20:55

PintofFizz · 29/06/2026 20:53

Emma's only 7 years older than her husband isn't she?

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I think they're referencing the film where Emma T plays a middle aged widow who engages the services of a hot young male sex worker.

PintofFizz · 29/06/2026 20:53

ProudCat · 29/06/2026 19:14

Two words: Emma Thompson.

Emma's only 7 years older than her husband isn't she?